diff --git a/conn.go b/conn.go
index 6aad628b..a037aff9 100644
--- a/conn.go
+++ b/conn.go
@@ -54,6 +54,7 @@ type Conn struct {
 	conn                net.Conn
 	isTLS               bool
 	isClosing           bool
+	closeErr            error
 	isStartingTLS       bool
 	Debug               debugging
 	chanConfirm         chan bool
@@ -298,6 +299,11 @@ func (l *Conn) processMessages() {
 			log.Printf("ldap: recovered panic in processMessages: %v", err)
 		}
 		for messageID, channel := range l.chanResults {
+			// If we are closing due to an error, inform anyone who
+			// is waiting about the error.
+			if l.isClosing && l.closeErr != nil {
+				channel <- &PacketResponse{Error: l.closeErr}
+			}
 			l.Debug.Printf("Closing channel for MessageID %d", messageID)
 			close(channel)
 			delete(l.chanResults, messageID)
@@ -324,15 +330,20 @@ func (l *Conn) processMessages() {
 			case MessageRequest:
 				// Add to message list and write to network
 				l.Debug.Printf("Sending message %d", message.MessageID)
-				l.chanResults[message.MessageID] = message.Channel
 
 				buf := message.Packet.Bytes()
 				_, err := l.conn.Write(buf)
 				if err != nil {
 					l.Debug.Printf("Error Sending Message: %s", err.Error())
+					message.Channel <- &PacketResponse{Error: fmt.Errorf("unable to send request: %s", err)}
+					close(message.Channel)
 					break
 				}
 
+				// Only add to chanResults if we were able to
+				// successfully write the message.
+				l.chanResults[message.MessageID] = message.Channel
+
 				// Add timeout if defined
 				if l.requestTimeout > 0 {
 					go func() {
@@ -397,6 +408,7 @@ func (l *Conn) reader() {
 		if err != nil {
 			// A read error is expected here if we are closing the connection...
 			if !l.isClosing {
+				l.closeErr = fmt.Errorf("unable to read LDAP response packet: %s", err)
 				l.Debug.Printf("reader error: %s", err.Error())
 			}
 			return
diff --git a/error_test.go b/error_test.go
index 4ec720d9..c010ebe3 100644
--- a/error_test.go
+++ b/error_test.go
@@ -1,7 +1,11 @@
 package ldap
 
 import (
+	"errors"
+	"net"
+	"strings"
 	"testing"
+	"time"
 
 	"gopkg.in/asn1-ber.v1"
 )
@@ -16,8 +20,8 @@ func TestNilPacket(t *testing.T) {
 
 	// Test for nil result
 	kids := []*ber.Packet{
-		&ber.Packet{}, // Unused
-		nil,           // Can't be nil
+		{},  // Unused
+		nil, // Can't be nil
 	}
 	pack := &ber.Packet{Children: kids}
 	code, _ = getLDAPResultCode(pack)
@@ -25,5 +29,74 @@ func TestNilPacket(t *testing.T) {
 	if code != ErrorUnexpectedResponse {
 		t.Errorf("Should have an 'ErrorUnexpectedResponse' error in nil packets, got: %v", code)
 	}
+}
+
+// TestConnReadErr tests that an unexpected error reading from underlying
+// connection bubbles up to the goroutine which makes a request.
+func TestConnReadErr(t *testing.T) {
+	conn := &signalErrConn{
+		signals: make(chan error),
+	}
+
+	ldapConn := NewConn(conn, false)
+	ldapConn.Start()
+
+	// Make a dummy search request.
+	searchReq := NewSearchRequest("dc=example,dc=com", ScopeWholeSubtree, DerefAlways, 0, 0, false, "(objectClass=*)", nil, nil)
+
+	expectedError := errors.New("this is the error you are looking for")
+
+	// Send the signal after a short amount of time.
+	time.AfterFunc(10*time.Millisecond, func() { conn.signals <- expectedError })
+
+	// This should block until the underlyiny conn gets the error signal
+	// which should bubble up through the reader() goroutine, close the
+	// connection, and
+	_, err := ldapConn.Search(searchReq)
+	if err == nil || !strings.Contains(err.Error(), expectedError.Error()) {
+		t.Errorf("not the expected error: %s", err)
+	}
+}
+
+// signalErrConn is a helful type used with TestConnReadErr. It implements the
+// net.Conn interface to be used as a connection for the test. Most methods are
+// no-ops but the Read() method blocks until it receives a signal which it
+// returns as an error.
+type signalErrConn struct {
+	signals chan error
+}
+
+// Read blocks until an error is sent on the internal signals channel. That
+// error is returned.
+func (c *signalErrConn) Read(b []byte) (n int, err error) {
+	return 0, <-c.signals
+}
+
+func (c *signalErrConn) Write(b []byte) (n int, err error) {
+	return len(b), nil
+}
+
+func (c *signalErrConn) Close() error {
+	close(c.signals)
+	return nil
+}
+
+func (c *signalErrConn) LocalAddr() net.Addr {
+	return (*net.TCPAddr)(nil)
+}
+
+func (c *signalErrConn) RemoteAddr() net.Addr {
+	return (*net.TCPAddr)(nil)
+}
+
+func (c *signalErrConn) SetDeadline(t time.Time) error {
+	return nil
+}
+
+func (c *signalErrConn) SetReadDeadline(t time.Time) error {
+	return nil
+}
 
+func (c *signalErrConn) SetWriteDeadline(t time.Time) error {
+	return nil
 }